Ethyl Bromide → 2-Ethoxybenzonitrile

HRID 1244214Notes

Reaction equation

HRID 1244214 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH3:17]>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:17]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile

Product 1

HCID 5769222-Ethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25 g (210 mmol) of 2-hydroxybenzonitrile are refluxed with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide in 500 ml of acetone overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colourless liquid.

Workup

  1. filtrationThe solid is filtered off
  2. customthe solvent is removed under reduced pressure
  3. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-a34b0a43998c40468030e5494d325d55
Source dataset
uspto-grants-2006_10
Patent number
US07122540B2

Reaction notes

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